Manufacture of vat dyestuffs.



nnirnn STATES PATENT OFFICE.

EDWARD WPAY, OF BIEBRICH ON-THE-RHINE, GERMANY, ASSIGNOB TO THE F KALLE AND COMPANY, AKTIENGESELLSCHAFT, OF IBIEBRICH-ON-THE-RHINE,

' GERMANY.

MANUFACTURE OF VAT DYESTUEFS.

No Drawing.

Patented Aug. 18, 1914.

To all whom it may concern Be it known that I, EDWARD WBAY, chemist, and a subjectof the King of England,

residin at 82 Rathausstrasse, Biebrich-onthe-Rhine, Germany, have invented certain new'and useful Improvements in the Manufacture of Vat Dyestuffs, of which the following is a specification.

In the specification of German Letters Patent No. 241997 a process for producing vat dye-stuffs is described which consists in combining phenooxynaphthocarbazoles derived from a-naphthylamin, with isatin-oe derivatives. The coloring matters obtained according to this known process dye the fiber gray to black tints. Now, I have found that blue to black-violet indigoid vat-dyestuffs of this kind can be produced by em loying in the condensation with the isatin-a-derivatives, those phenooxynaphthocarbazoles which derive from fi-napththylainin and have the following formula:

Rey/

5 Where R is the radical of an oxynaphthalene having a free ortho position to the hydroxyl group.

Example: 3 parts of 5-chloro-isatin-2-pchloranilid are heated in about 25 parts by Weight of acetic anhydrid with 2.3 parts of 2.1-pheno-5-oxynaphthocarbazole of the following formula:

which have been obtained by fusing the carbazole from phenylhydrazin and Q-aminonaphthalene-5-sulfonic acid with caustic alkali. After cooling, the mass is filtered and washed with alcohol.

The produced dye-stuff is in dry state a violet powder, soluble in sulfuric acid with a grayish blue color. It has the following graphically represented constitution:

Reduced, it forms a goldish-yellow vat from which the textile fiber is dyed in dark blue tints becoming purer and redder on soaping or acidifying. Instead of 5-chloroisatimQ-p-chloranilid other reactive isatin-ozderivatives, their substitution products,

homologues or analogues may be employed,

and also other derivatives of the used phenooxynaphthocarbazole having a free ortho position next to the hydroxyl group.

The dye-stuffs obtained accordlng to the present process may be halogenated in the usual manner f. i. by treating with bromin in the presence of nitrobenzenc, sulfuric acid or other solvents or diluents.

The products of the present invention including the halogen-containing and halogenated products have a constitution graphically represented as follows:

Where R is the oxynaphthalene nucleus having a free ortho osition to the oxy group,

and R is the radical of the alpha-isatin derivative, e. 9., the halogenated derivative.

I claim:

1. Process for producing vat dyestuffs which consists in treating phenooxynaphthocarbazoles deriving from fi-naphthylamin with the reactive isatin-a-derivatives.

2. Process for producing vat dye-stuffs which consists in treating 2.1-pheno-5-oxynaphtliocarbazole with 5-chloro-isatin-2-pchloranilid.

3. As new products the vat dye-stuffs obtainable by condensation of phenooxynaphthocarbazoles derived from (B-naphthylamin with thereective isetin-cederivetives, hav ing the tollowmg graphically represented constitution x a! Where It is the radical of an oxynephtlielene and R an isetln radical 1n ortho position to the oxy group hem blue to v1olet-bleck dyestuffs insoluble in t e usual solvents and bewhere R is the radical of an oivzynephthalene and R the isetin radical in ortlio position to meeeee the my group being blue to violethlscl: dyestufis insoluble in the usual solvents and being reduced m treatment with reducing agents to leuco compounds, from which the dyestufis are regenerated by oxidizing agents.

5. As a, new product the vet dye-stun? elf the following formula:

being in dry state e pewder insoluble in the usual solvents, soluble in sulfuric acid with a grayish-blue color being reduced on treat ment with. reducing agents to e goldi'shyellow vat from which the textile fiber is dyed violet shades.

In testimony whereof I have signed my name to this specification in the presence of two subscribing witnesses.

EDW W,

Witnesses M01211; lll n'rzne, MARIA HAHN Be lies at this patent be ebteiaxed. for five cents each, by addressing the Commissioner of fat-ants,

"Washington D. (2. 

